#------------------------------------------------------------------------------ #$Date: 2020-04-22 23:50:26 +0300 (Wed, 22 Apr 2020) $ #$Revision: 251055 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557860.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557860 loop_ _publ_author_name 'Yuan, Jie' 'Wang, Yongrong' 'Li, Ling' 'Wang, Shuang' 'Tang, Xingxing' 'Wang, Honglei' 'Li, Mingguang' 'Zheng, Chao' 'Chen, Runfeng' _publ_section_title ; Activating Intersystem Crossing and Aggregation Coupling by CN-Substitution for Efficient Organic Ultralong Room Temperature Phosphorescence ; _journal_name_full 'The Journal of Physical Chemistry C' _journal_paper_doi 10.1021/acs.jpcc.0c01762 _journal_year 2020 _chemical_formula_moiety 'C8 H4 N2' _chemical_formula_sum 'C8 H4 N2' _chemical_formula_weight 128.13 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-01-20 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324) ; _cell_angle_alpha 114.297(13) _cell_angle_beta 92.785(15) _cell_angle_gamma 97.812(16) _cell_formula_units_Z 1 _cell_length_a 3.781(3) _cell_length_b 6.450(5) _cell_length_c 7.270(5) _cell_measurement_reflns_used 150 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 0.959 _cell_measurement_theta_min 0.904 _cell_volume 159.0(2) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.01 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.957 _diffrn_measured_fraction_theta_max 0.822 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX-II CCD' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_unetI/netI 0.0412 _diffrn_reflns_Laue_measured_fraction_full 0.957 _diffrn_reflns_Laue_measured_fraction_max 0.822 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2056 _diffrn_reflns_point_group_measured_fraction_full 0.957 _diffrn_reflns_point_group_measured_fraction_max 0.822 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 37.902 _diffrn_reflns_theta_min 3.095 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 0.084 _exptl_crystal_density_diffrn 1.338 _exptl_crystal_description block _exptl_crystal_F_000 66 _exptl_crystal_size_max 2 _exptl_crystal_size_mid 1 _exptl_crystal_size_min 0.5 _refine_diff_density_max 0.468 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 46 _refine_ls_number_reflns 1414 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0503 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.0317P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1362 _refine_ls_wR_factor_ref 0.1415 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1282 _reflns_number_total 1414 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jp0c01762_si_004.cif _cod_data_source_block 1 _cod_original_cell_volume 159.02(19) _cod_database_code 1557860 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.959 _shelx_estimated_absorpt_t_min 0.850 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C004(H004), C005(H005) ; _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P-1 REM Old TITL 1 in P-1 REM SHELXT solution in P-1 REM R1 0.100, Rweak 0.004, Alpha 0.043, Orientation as input REM Formula found by SHELXT: C4 N CELL 0.71073 3.7812 6.4496 7.27 114.297 92.785 97.812 ZERR 1 0.0026 0.0045 0.0049 0.013 0.015 0.016 LATT 1 SFAC C H N UNIT 8 4 2 L.S. 10 PLAN 20 SIZE 0.5 1 2 TEMP -173.14 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.074800 0.031700 FVAR 7.56633 C002 1 0.376026 0.404635 0.296747 11.00000 0.01570 0.01751 = 0.01236 0.00600 -0.00014 0.00242 C003 1 0.243236 0.303793 0.084999 11.00000 0.02105 0.01920 = 0.01495 0.00682 -0.00038 0.00358 C004 1 0.363295 0.636194 0.414618 11.00000 0.01929 0.01765 = 0.01476 0.00754 -0.00028 0.00432 AFIX 43 H004 2 0.270132 0.727099 0.355380 11.00000 -1.20000 AFIX 0 C005 1 0.488093 0.732003 0.619042 11.00000 0.02003 0.01627 = 0.01468 0.00552 0.00007 0.00417 AFIX 43 H005 2 0.481523 0.889776 0.701778 11.00000 -1.20000 AFIX 0 N001 3 0.135067 0.221309 -0.084797 11.00000 0.03270 0.02398 = 0.01594 0.00653 -0.00331 0.00569 HKLF 4 REM 1_a.res in P-1 REM R1 = 0.0503 for 1282 Fo > 4sig(Fo) and 0.0550 for all 1414 data REM 46 parameters refined using 0 restraints END WGHT 0.0748 0.0318 REM Highest difference peak 0.468, deepest hole -0.302, 1-sigma level 0.066 Q1 1 0.4137 0.3437 0.3527 11.00000 0.05 0.47 Q2 1 0.3324 0.5078 0.3556 11.00000 0.05 0.40 Q3 1 0.4158 0.6831 0.5217 11.00000 0.05 0.33 Q4 1 0.2191 0.2873 -0.0016 11.00000 0.05 0.32 Q5 1 0.3585 0.3485 0.1948 11.00000 0.05 0.21 Q6 1 0.8779 0.9689 0.6644 11.00000 0.05 0.17 Q7 1 0.3393 0.8191 0.6682 11.00000 0.05 0.17 Q8 1 0.7441 0.9644 0.9143 11.00000 0.05 0.16 Q9 1 -0.0386 0.2199 -0.1863 11.00000 0.05 0.16 Q10 1 -0.0521 0.1051 -0.1673 11.00000 0.05 0.15 Q11 1 0.1793 0.2457 -0.2005 11.00000 0.05 0.15 Q12 1 -0.0911 0.7119 0.2779 11.00000 0.05 0.15 Q13 1 0.1872 0.3971 -0.0757 11.00000 0.05 0.15 Q14 1 0.7335 0.7604 0.5444 11.00000 0.05 0.14 Q15 1 0.0774 0.4354 0.2015 11.00000 0.05 0.14 Q16 1 0.6558 0.8676 0.6829 11.00000 0.05 0.13 Q17 1 0.5734 0.4049 0.1779 11.00000 0.05 0.13 Q18 1 0.3743 0.1011 0.0534 11.00000 0.05 0.13 Q19 1 0.2326 0.5782 0.0961 11.00000 0.05 0.13 Q20 1 0.4273 0.4251 0.1825 11.00000 0.05 0.13 ; _shelx_res_checksum 66723 _shelx_hkl_file ; -2 0 0 140.69 6.60 4 0 0 204.98 10.00 5 0 0 2.00 3.20 5 0 0 3.70 2.20 5 0 0 3.40 3.60 6 0 0 16.30 5.10 5 -1 0 82.09 6.60 5 -1 0 87.69 5.70 5 -1 0 81.39 5.90 4 -1 0 112.59 6.00 4 -1 0 104.09 6.00 -3 1 0 1777.02 73.89 -2 1 0 5952.80 244.68 1 1 0 269.87 17.70 1 1 0 316.87 12.60 2 1 0 2001.30 82.99 3 1 0 259.47 12.00 4 1 0 376.96 17.20 5 1 0 125.59 7.80 6 1 0 -7.40 5.20 5 -2 0 10.90 2.40 5 -2 0 15.40 2.90 5 -2 0 16.80 3.50 4 -2 0 219.28 10.20 4 -2 0 201.38 10.30 -4 2 0 200.28 9.90 3 -2 0 3635.04 154.68 3 -2 0 3841.42 154.78 -3 2 0 3761.52 154.58 2 -2 0 222.58 10.20 -2 2 0 230.68 10.10 1 -2 0 93.99 4.10 1 -2 0 81.99 4.00 1 -2 0 85.79 4.20 -1 2 0 95.19 4.20 1 2 0 68.29 3.50 2 2 0 51.39 3.30 3 2 0 672.43 29.00 4 2 0 420.96 19.20 5 2 0 391.76 18.60 6 -3 0 2.50 3.60 5 -3 0 60.99 5.30 4 -3 0 29.20 3.20 4 -3 0 24.30 3.90 -4 3 0 21.90 3.10 3 -3 0 1053.69 44.20 3 -3 0 1072.19 44.50 -3 3 0 1032.50 44.20 2 -3 0 4198.28 172.28 2 -3 0 4064.79 172.68 -2 3 0 4309.47 172.58 0 -3 0 4352.66 178.98 1 3 0 277.97 12.30 2 3 0 531.35 23.00 3 3 0 8.20 1.80 4 3 0 63.59 5.20 5 3 0 19.00 3.70 6 -4 0 -0.20 3.60 5 -4 0 3.50 2.70 4 -4 0 1066.49 45.90 -4 4 0 1076.69 45.40 3 -4 0 8375.86 338.17 3 -4 0 8177.78 338.87 -3 4 0 8135.89 338.37 2 -4 0 481.65 20.80 2 -4 0 484.25 20.20 -2 4 0 471.65 20.50 1 -4 0 304.67 13.20 1 -4 0 314.27 13.00 -1 4 0 292.57 13.20 0 -4 0 82.89 4.10 0 -4 0 82.39 4.30 0 4 0 82.49 4.10 1 4 0 952.00 40.00 2 4 0 7.50 1.40 3 4 0 122.99 7.00 4 4 0 662.43 29.50 6 -5 0 135.29 11.00 5 -5 0 40.20 5.80 4 -5 0 1753.12 73.99 3 -5 0 1125.39 47.50 -3 5 0 1112.49 47.10 2 -5 0 -0.90 1.00 2 -5 0 0.70 1.10 -2 5 0 0.50 1.20 1 -5 0 864.71 35.90 1 -5 0 813.62 36.00 -1 5 0 891.21 36.20 0 -5 0 124.19 5.80 0 -5 0 113.39 6.10 0 5 0 118.69 5.90 1 5 0 286.67 12.90 2 5 0 95.29 5.50 3 5 0 23.80 3.90 4 5 0 1246.58 53.69 5 -6 0 -3.10 3.10 4 -6 0 1.10 2.50 3 -6 0 862.41 37.10 2 -6 0 6.20 1.50 1 -6 0 41.80 3.10 1 -6 0 40.30 3.10 -1 6 0 33.30 3.70 0 -6 0 520.85 22.90 0 6 0 545.65 23.10 1 6 0 485.05 21.20 2 6 0 942.61 40.40 3 6 0 32.70 4.80 5 -7 0 65.89 8.10 4 -7 0 544.45 24.90 3 -7 0 470.55 21.40 2 -7 0 69.39 4.90 1 -7 0 172.28 8.30 -1 7 0 158.28 8.90 0 7 0 -1.90 1.80 1 7 0 191.38 9.70 2 7 0 2.40 2.20 3 7 0 8.60 4.60 4 -8 0 26.80 4.40 3 -8 0 7.80 3.00 2 -8 0 108.99 7.10 1 -8 0 28.80 4.30 -1 8 0 38.70 7.10 0 8 0 94.59 7.30 1 8 0 448.56 20.80 2 8 0 809.92 35.70 3 -9 0 27.30 4.50 2 -9 0 56.19 6.30 1 -9 0 7.90 3.70 1 9 0 924.21 42.50 2 -10 1 41.50 7.70 1 9 -1 25.20 4.30 0 9 -1 1.80 3.70 1 -9 1 98.59 7.40 2 -9 1 0.80 2.90 3 -9 1 3.20 3.30 2 8 -1 -0.60 2.60 1 8 -1 16.40 3.10 0 8 -1 32.30 5.20 -1 8 -1 92.39 6.70 1 -8 1 85.79 5.80 2 -8 1 194.38 10.10 3 -8 1 378.66 17.80 4 -8 1 302.37 15.50 3 7 -1 304.67 15.20 2 7 -1 251.27 12.40 1 7 -1 172.98 9.00 0 7 -1 130.99 7.30 -1 7 -1 67.99 5.30 1 -7 1 65.99 4.40 -2 7 -1 1661.43 69.29 2 -7 1 1636.44 69.09 3 -7 1 173.38 9.30 4 -7 1 35.50 5.10 5 -7 1 158.58 10.20 3 6 -1 295.07 14.40 2 6 -1 294.97 13.80 1 6 -1 182.48 8.80 0 6 -1 345.17 15.00 0 -6 1 321.67 14.80 -1 6 -1 55.59 4.20 1 -6 1 53.49 3.50 -2 6 -1 34.50 3.70 2 -6 1 50.79 3.40 -3 6 -1 953.30 40.90 3 -6 1 964.10 41.00 4 -6 1 281.87 13.90 5 -6 1 458.05 21.40 4 5 -1 12.70 2.90 3 5 -1 0.50 1.70 2 5 -1 298.07 13.60 1 5 -1 95.99 5.00 0 5 -1 79.99 4.60 0 -5 1 87.89 4.40 -1 5 -1 299.07 15.30 1 -5 1 367.06 15.20 1 -5 1 372.76 14.90 -2 5 -1 8187.08 354.16 2 -5 1 9042.09 354.26 -3 5 -1 1554.84 67.49 3 -5 1 1668.13 67.59 -4 5 -1 108.79 6.80 4 -5 1 101.89 6.50 5 -5 1 6.20 2.80 6 -5 1 23.90 4.50 4 4 -1 19.60 3.80 3 4 -1 133.19 7.20 2 4 -1 242.48 11.20 1 4 -1 599.34 25.50 0 4 -1 3056.79 128.59 0 -4 1 3183.08 128.49 -1 4 -1 6445.95 256.17 1 -4 1 6010.90 255.97 -2 4 -1 5405.86 219.58 2 -4 1 5255.87 219.48 -4 4 -1 193.08 9.80 4 -4 1 185.08 9.60 5 -4 1 -0.10 2.50 5 3 -1 126.19 8.00 4 3 -1 122.19 7.20 3 3 -1 174.78 8.70 2 3 -1 200.88 9.30 0 3 -1 317.17 13.20 0 -3 1 297.97 13.10 -1 3 -1 3708.23 152.78 1 -3 1 3712.23 152.68 -2 3 -1 3320.37 135.79 2 -3 1 3242.68 135.59 2 -3 1 3301.57 135.19 -3 3 -1 97.69 5.60 3 -3 1 92.29 5.30 3 -3 1 91.79 4.90 -4 3 -1 9.30 2.10 4 -3 1 10.40 2.00 -5 3 -1 182.08 9.90 5 -3 1 169.68 9.40 6 2 -1 140.99 13.60 5 2 -1 202.58 10.80 4 2 -1 139.99 7.50 3 2 -1 235.98 11.00 2 2 -1 667.53 28.30 1 2 -1 230.08 10.20 2 -2 1 3481.95 143.39 -3 2 -1 122.89 6.60 3 -2 1 126.39 6.30 -4 2 -1 274.07 13.00 4 -2 1 264.47 12.60 4 -2 1 284.07 13.30 5 -2 1 23.50 3.80 5 -2 1 26.90 4.90 6 1 -1 23.80 5.30 5 1 -1 96.09 8.30 5 1 -1 99.29 6.40 4 1 -1 33.40 3.00 3 1 -1 122.69 6.20 2 1 -1 2274.37 93.99 1 -1 1 6331.47 260.07 -2 1 -1 34.60 2.60 2 -1 1 32.60 2.10 -3 1 -1 504.25 21.40 3 -1 1 474.45 21.00 -4 1 -1 3.80 1.60 4 -1 1 3.80 1.50 5 -1 1 62.29 5.70 6 0 -1 20.90 4.80 5 0 -1 54.29 4.50 5 0 -1 49.80 5.80 4 0 -1 210.58 10.30 4 0 -1 230.88 11.50 3 0 -1 662.23 28.20 0 0 -1 103.29 4.40 0 0 -1 105.49 4.40 0 0 1 89.39 4.40 -1 0 -1 4886.61 200.98 -2 0 -1 238.18 10.80 -3 0 -1 603.94 26.20 4 0 1 7.30 20.70 4 0 1 8.60 1.80 4 0 1 7.20 1.80 5 0 1 14.80 27.80 5 0 1 37.70 5.00 6 0 1 836.42 42.30 5 -1 -1 161.98 9.40 5 -1 -1 162.48 8.90 4 -1 -1 1973.50 80.89 4 -1 -1 1875.01 79.99 3 -1 -1 17.50 2.70 2 -1 -1 2089.29 85.99 -2 1 1 2060.79 85.49 0 -1 -1 97.59 4.20 0 -1 -1 103.69 4.30 0 1 1 85.49 4.20 0 1 1 98.19 4.30 -1 -1 -1 157.18 6.80 -1 -1 -1 140.89 6.80 -2 -1 -1 3302.47 136.49 4 1 1 824.32 35.80 5 1 1 31.20 5.00 6 -2 -1 0.60 3.50 5 -2 -1 105.99 6.90 5 -2 -1 107.59 7.20 4 -2 -1 2.10 1.30 4 -2 -1 2.80 1.80 4 -2 -1 0.80 1.50 3 -2 -1 1261.77 49.10 3 -2 -1 1093.89 48.90 -3 2 1 1130.59 48.30 2 -2 -1 5424.36 216.88 2 -2 -1 4907.51 216.88 2 -2 -1 5396.56 216.38 -2 2 1 5347.56 216.48 0 -2 -1 21.90 1.20 0 -2 -1 17.00 1.40 -1 -2 -1 1635.24 69.69 1 2 1 1707.73 69.69 2 2 1 58.49 3.60 2 2 1 50.19 14.50 3 2 1 920.11 54.59 3 2 1 749.13 35.70 4 2 1 143.29 8.30 5 2 1 40.20 5.50 6 -3 -1 10.30 3.90 5 -3 -1 323.07 15.80 4 -3 -1 3822.62 156.18 4 -3 -1 3716.33 156.38 3 -3 -1 279.87 13.40 3 -3 -1 295.87 13.20 -3 3 1 290.67 12.60 2 -3 -1 2166.38 86.99 2 -3 -1 2120.59 87.49 2 -3 -1 2074.19 87.69 -2 3 1 2093.19 87.19 1 -3 -1 31.90 2.20 1 -3 -1 34.90 2.20 -1 3 1 34.40 2.10 0 -3 -1 2302.57 94.29 0 -3 -1 2175.18 93.99 0 3 1 2367.36 94.09 -1 -3 -1 -1.20 1.00 1 3 1 -1.50 0.90 2 3 1 288.77 13.20 3 3 1 241.88 11.80 4 3 1 1182.28 50.79 5 3 1 -4.10 5.00 6 -4 -1 -0.50 3.90 5 -4 -1 1412.96 60.39 4 -4 -1 1995.80 83.89 3 -4 -1 7.20 1.70 -3 4 1 6.40 1.30 2 -4 -1 530.55 22.60 2 -4 -1 528.45 22.20 -2 4 1 504.25 22.00 1 -4 -1 49.30 3.10 1 -4 -1 50.19 3.10 -1 4 1 57.69 3.20 0 -4 -1 455.25 19.40 0 -4 -1 448.36 19.10 0 4 1 444.86 19.10 -1 -4 -1 42.90 3.50 1 4 1 43.30 2.90 2 4 1 211.18 10.30 3 4 1 3274.87 136.39 4 4 1 1193.78 51.59 5 -5 -1 148.99 9.60 4 -5 -1 110.29 7.40 3 -5 -1 13.80 2.90 3 -5 -1 14.80 2.80 2 -5 -1 18.30 2.00 2 -5 -1 14.10 2.30 -2 5 1 17.70 2.30 1 -5 -1 662.43 28.30 1 -5 -1 657.43 28.30 -1 5 1 677.03 28.20 0 -5 -1 282.47 13.60 0 -5 -1 305.57 13.20 0 5 1 311.87 13.30 1 5 1 935.31 39.50 2 5 1 240.18 11.60 3 5 1 1090.99 47.00 4 5 1 2.30 3.50 5 -6 -1 317.17 16.40 4 -6 -1 491.25 22.70 3 -6 -1 28.70 3.90 2 -6 -1 291.17 13.00 2 -6 -1 284.67 13.30 1 -6 -1 105.09 6.00 1 -6 -1 113.19 5.80 -1 6 1 102.99 6.00 0 -6 -1 808.32 33.50 0 -6 -1 781.72 34.00 0 6 1 783.12 33.60 1 6 1 257.17 12.00 2 6 1 72.79 5.40 3 6 1 331.47 16.20 4 -7 -1 39.50 6.10 3 -7 -1 96.49 6.90 2 -7 -1 8.80 2.20 1 -7 -1 58.69 4.80 1 -7 -1 63.89 4.70 -1 7 1 71.99 6.30 0 -7 -1 85.99 5.50 0 7 1 78.19 5.70 1 7 1 838.02 36.00 2 7 1 32.50 4.90 4 -8 -1 14.20 4.50 3 -8 -1 33.50 6.00 2 -8 -1 23.20 5.10 1 -8 -1 190.78 10.30 1 8 1 659.23 29.40 3 -9 -1 87.09 9.00 2 -9 -1 103.89 8.00 1 -9 -1 197.78 11.60 0 10 -2 27.40 6.90 2 -10 2 45.30 6.90 1 9 -2 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466.25 20.70 -3 3 -7 185.58 11.00 -4 3 -7 315.37 17.40 5 2 -7 87.59 9.20 4 2 -7 309.67 16.30 3 2 -7 609.34 27.80 2 2 -7 208.08 9.50 2 2 -7 164.58 9.90 1 2 -7 71.29 5.20 1 2 -7 75.49 5.30 0 2 -7 1448.46 60.29 0 2 -7 1409.36 59.99 -1 2 -7 197.68 9.40 -1 2 -7 200.78 10.20 -3 2 -7 1192.68 51.89 -4 2 -7 272.07 15.70 5 1 -7 1.00 4.50 4 1 -7 16.60 4.00 3 1 -7 91.59 7.10 2 1 -7 60.59 5.10 1 1 -7 3098.19 129.19 1 1 -7 3112.09 128.39 0 1 -7 339.07 15.40 0 1 -7 330.47 15.20 -1 1 -7 37.10 3.10 -1 1 -7 34.70 4.00 -2 1 -7 680.83 30.40 -2 1 -7 679.83 29.60 -3 1 -7 94.19 6.70 -3 1 -7 94.49 7.80 -4 1 -7 74.69 9.10 5 0 -7 67.49 8.80 4 0 -7 814.92 36.80 3 0 -7 2107.19 89.09 2 0 -7 138.89 8.50 1 0 -7 526.15 23.50 0 0 -7 92.29 6.00 0 0 -7 97.59 5.60 -1 0 -7 399.46 18.20 -1 0 -7 387.86 17.80 -2 0 -7 5.70 2.00 -2 0 -7 3.10 2.90 -3 0 -7 312.37 16.40 -3 0 -7 336.97 16.90 5 -1 -7 106.09 10.40 4 -1 -7 1645.54 70.79 3 -1 -7 521.35 24.50 2 -1 -7 21.10 4.30 1 -1 -7 318.37 15.00 0 -1 -7 275.97 13.10 -1 -1 -7 331.47 15.50 -1 -1 -7 331.47 15.60 -2 -1 -7 208.68 11.50 -2 -1 -7 196.78 10.80 3 1 7 576.84 27.00 5 -2 -7 32.60 7.00 4 -2 -7 19.70 4.60 4 -2 -7 17.50 4.60 3 -2 -7 218.78 11.90 3 -2 -7 202.48 12.00 2 -2 -7 108.59 7.10 2 -2 -7 98.89 7.00 1 -2 -7 31.90 3.90 1 -2 -7 31.60 3.60 0 -2 -7 1263.47 53.89 -1 -2 -7 257.07 12.80 1 2 7 241.78 12.50 -2 -2 -7 71.39 6.50 2 2 7 75.09 7.40 4 -3 -7 513.25 24.50 4 -3 -7 507.75 24.50 3 -3 -7 138.09 8.90 3 -3 -7 129.29 9.50 2 -3 -7 0.40 2.70 2 -3 -7 4.10 2.60 1 -3 -7 452.65 21.00 0 -3 -7 157.08 9.20 -1 -3 -7 232.08 12.60 -2 -3 -7 18.30 4.30 2 3 7 16.60 4.20 4 -4 -7 93.89 10.80 4 -4 -7 129.49 9.50 3 -4 -7 4.40 3.30 3 -4 -7 0.70 4.10 2 -4 -7 105.49 7.50 1 -4 -7 5.10 2.90 0 -4 -7 187.78 11.00 -1 -4 -7 183.28 11.80 -2 -4 -7 216.18 14.30 3 -5 -7 63.69 7.80 2 -5 -7 52.29 6.90 1 -5 -7 154.28 10.20 0 -5 -7 470.75 23.30 0 9 -8 139.19 10.70 -1 9 -8 365.06 19.50 3 8 -8 13.60 4.60 2 8 -8 85.39 8.90 1 8 -8 9.60 4.10 0 8 -8 119.69 9.10 -1 8 -8 2144.99 91.29 -2 8 -8 1010.10 45.60 3 7 -8 119.99 9.70 3 7 -8 122.79 10.10 2 7 -8 261.47 13.80 2 7 -8 250.77 13.90 1 7 -8 499.85 23.50 0 7 -8 91.19 7.40 -1 7 -8 504.65 24.00 -2 7 -8 133.89 10.70 -3 7 -8 19.20 6.30 4 6 -8 11.10 5.10 3 6 -8 16.50 3.90 3 6 -8 18.00 4.40 2 6 -8 162.98 9.90 2 6 -8 166.88 10.10 1 6 -8 32.20 4.50 0 6 -8 58.49 5.80 -1 6 -8 1493.65 64.19 -2 6 -8 579.24 27.30 -3 6 -8 32.90 6.20 4 5 -8 2.10 4.00 3 5 -8 97.69 8.00 2 5 -8 560.64 24.50 2 5 -8 518.15 24.60 1 5 -8 2195.68 94.09 1 5 -8 2303.67 94.39 0 5 -8 82.39 6.10 0 5 -8 77.89 5.40 -1 5 -8 1458.15 62.59 -2 5 -8 0.50 3.80 -3 5 -8 98.29 9.60 4 4 -8 -0.20 3.70 3 4 -8 250.17 13.80 2 4 -8 3708.33 151.68 2 4 -8 3604.84 152.38 1 4 -8 1873.51 78.89 1 4 -8 1884.41 78.89 0 4 -8 133.89 7.20 0 4 -8 125.79 7.90 -1 4 -8 170.38 10.20 -1 4 -8 173.48 8.40 -2 4 -8 37.90 6.50 -3 4 -8 274.37 15.70 4 3 -8 139.09 10.30 3 3 -8 247.48 13.60 2 3 -8 795.02 35.20 1 3 -8 219.28 10.70 1 3 -8 205.88 11.00 0 3 -8 125.69 7.90 0 3 -8 130.49 7.10 -1 3 -8 37.80 3.20 -1 3 -8 35.70 5.00 -2 3 -8 1324.07 57.29 -3 3 -8 235.68 13.70 4 2 -8 0.30 3.90 3 2 -8 18.20 4.00 2 2 -8 1238.98 53.29 1 2 -8 482.65 21.40 1 2 -8 478.45 21.90 0 2 -8 134.59 7.70 0 2 -8 131.09 7.10 -1 2 -8 887.11 37.10 -1 2 -8 848.92 37.90 -2 2 -8 519.75 22.60 -2 2 -8 492.25 23.80 -3 2 -8 294.27 14.50 -3 2 -8 285.67 16.00 4 1 -8 474.75 23.40 3 1 -8 152.68 10.00 2 1 -8 1097.39 47.70 1 1 -8 23.10 3.80 0 1 -8 213.58 10.50 -1 1 -8 50.19 5.60 -1 1 -8 60.49 4.40 -2 1 -8 112.29 7.10 -2 1 -8 117.89 8.60 -3 1 -8 32.90 7.30 -3 1 -8 29.20 5.90 4 0 -8 387.06 20.00 3 0 -8 75.89 7.60 2 0 -8 55.89 5.70 1 0 -8 52.99 4.70 0 0 -8 250.77 12.20 -1 0 -8 452.15 20.90 -1 0 -8 452.15 20.60 -2 0 -8 741.13 33.90 -2 0 -8 796.12 34.40 -3 0 -8 1620.84 70.29 -3 0 -8 1651.23 70.49 4 -1 -8 -0.90 4.60 3 -1 -8 49.60 6.60 2 -1 -8 -0.40 2.80 1 -1 -8 931.01 40.40 0 -1 -8 93.49 6.30 -1 -1 -8 18.90 4.10 -2 -1 -8 894.61 37.80 2 1 8 801.12 37.60 4 -2 -8 63.59 9.00 4 -2 -8 60.89 8.40 3 -2 -8 14.00 4.20 3 -2 -8 7.70 3.70 2 -2 -8 434.46 20.90 2 -2 -8 469.75 21.30 1 -2 -8 440.66 20.60 0 -2 -8 299.87 15.00 -1 -2 -8 59.59 6.10 -2 -2 -8 123.39 9.30 3 -3 -8 68.89 7.00 3 -3 -8 54.19 8.10 2 -3 -8 42.90 5.90 1 -3 -8 13.90 3.30 0 -3 -8 0.30 3.00 -1 -3 -8 87.89 8.10 -2 -3 -8 243.88 18.30 2 -4 -8 177.88 11.30 1 -4 -8 435.76 21.40 0 -4 -8 984.40 43.90 1 8 -9 207.08 13.10 0 8 -9 1035.60 46.00 -1 8 -9 12.60 5.40 -2 8 -9 20.00 8.10 3 7 -9 148.39 11.40 2 7 -9 83.19 8.00 1 7 -9 97.99 8.30 0 7 -9 311.77 16.20 -1 7 -9 338.87 18.20 -2 7 -9 82.99 9.90 3 6 -9 31.10 7.50 2 6 -9 385.76 18.40 2 6 -9 353.06 18.30 1 6 -9 86.59 6.50 0 6 -9 1613.94 69.09 -1 6 -9 6.80 4.50 -2 6 -9 31.30 6.10 -3 6 -9 120.79 12.60 4 5 -9 142.99 11.90 3 5 -9 1398.26 60.79 2 5 -9 1022.20 44.90 2 5 -9 1027.50 44.70 1 5 -9 264.77 13.60 1 5 -9 281.27 14.20 0 5 -9 6.00 2.10 0 5 -9 5.40 3.80 -1 5 -9 3.10 4.30 -2 5 -9 208.78 13.30 -3 5 -9 162.38 13.40 4 4 -9 259.67 15.50 3 4 -9 1075.79 47.60 2 4 -9 3.10 3.00 1 4 -9 22.00 4.50 1 4 -9 27.30 5.30 0 4 -9 106.99 6.40 0 4 -9 103.89 8.10 -1 4 -9 911.41 38.40 -1 4 -9 892.51 40.20 -2 4 -9 97.69 9.00 -3 4 -9 86.29 9.90 4 3 -9 41.50 8.00 3 3 -9 145.79 10.00 2 3 -9 226.78 12.40 1 3 -9 150.58 8.90 0 3 -9 580.84 25.60 0 3 -9 584.54 26.50 -1 3 -9 950.90 43.20 -1 3 -9 1013.00 41.90 -2 3 -9 278.97 15.40 -2 3 -9 276.27 13.60 -3 3 -9 37.10 6.30 4 2 -9 71.59 8.80 3 2 -9 818.82 37.00 1 2 -9 71.59 5.80 0 2 -9 347.67 16.20 0 2 -9 349.67 16.80 -1 2 -9 4.50 2.20 -2 2 -9 120.29 9.60 -2 2 -9 111.89 7.50 -3 2 -9 13.30 5.90 4 1 -9 104.09 10.20 3 1 -9 5.90 4.00 2 1 -9 0.10 3.00 1 1 -9 183.58 10.10 0 1 -9 327.87 15.50 -1 1 -9 533.95 25.20 -1 1 -9 550.24 24.40 -2 1 -9 1010.40 44.30 -2 1 -9 1024.90 45.00 -3 1 -9 192.48 12.20 4 0 -9 -6.70 5.00 3 0 -9 12.60 4.30 2 0 -9 406.86 19.80 1 0 -9 10.50 2.80 0 0 -9 287.37 14.30 -1 0 -9 1419.46 60.59 -2 0 -9 1877.31 80.99 -2 0 -9 1932.81 81.09 -3 0 -9 8.10 4.60 3 -1 -9 216.18 13.00 2 -1 -9 503.65 23.70 1 -1 -9 157.08 9.40 0 -1 -9 4.10 2.70 -1 -1 -9 619.24 28.40 -2 -1 -9 -2.90 3.60 3 -2 -9 137.59 10.20 3 -2 -9 124.99 10.50 2 -2 -9 41.20 6.30 1 -2 -9 111.29 8.40 0 -2 -9 15.20 3.70 -1 -2 -9 161.98 11.00 2 -3 -9 165.48 11.40 1 -3 -9 357.76 18.60 0 -3 -9 44.10 7.90 0 8 -10 147.69 17.00 3 7 -10 13.10 5.80 1 7 -10 799.22 36.20 0 7 -10 16.80 5.40 -1 7 -10 4.30 6.10 3 6 -10 252.47 15.10 2 6 -10 240.28 13.50 1 6 -10 177.48 11.60 0 6 -10 8.20 5.20 -1 6 -10 162.78 12.10 -2 6 -10 72.99 11.00 3 5 -10 33.30 7.90 2 5 -10 1.90 3.70 1 5 -10 50.29 6.00 0 5 -10 332.17 17.70 -1 5 -10 18.10 5.90 -2 5 -10 357.66 19.90 3 4 -10 27.90 5.40 2 4 -10 86.39 8.00 1 4 -10 199.98 11.20 0 4 -10 874.51 37.80 0 4 -10 881.51 39.30 -1 4 -10 96.99 9.90 -2 4 -10 2.20 5.40 3 3 -10 -5.70 3.90 2 3 -10 6.20 3.70 1 3 -10 511.15 23.70 0 3 -10 179.98 9.70 -1 3 -10 316.17 17.40 -1 3 -10 329.47 15.50 -2 3 -10 9.50 5.10 2 2 -10 110.09 8.60 1 2 -10 54.59 5.60 0 2 -10 136.39 8.40 -1 2 -10 236.88 17.00 -1 2 -10 213.98 11.80 -2 2 -10 59.69 9.40 -2 2 -10 79.79 7.10 3 1 -10 97.89 9.30 2 1 -10 0.10 3.20 1 1 -10 493.15 22.90 0 1 -10 1243.98 53.39 -1 1 -10 2006.30 84.79 -2 1 -10 5.80 4.10 3 0 -10 242.58 14.60 2 0 -10 25.60 5.80 1 0 -10 89.99 7.30 0 0 -10 1262.17 54.59 -1 0 -10 213.38 12.30 -2 0 -10 35.70 7.40 2 -1 -10 142.79 10.20 1 -1 -10 13.50 3.90 0 -1 -10 8.90 3.60 -1 -1 -10 443.96 22.20 2 6 -11 -2.20 4.60 0 6 -11 13.70 6.40 -1 6 -11 395.86 22.50 3 5 -11 9.00 6.90 2 5 -11 30.90 5.60 1 5 -11 399.86 19.20 -1 5 -11 157.98 13.00 3 4 -11 -5.80 5.20 2 4 -11 356.96 18.50 1 4 -11 261.47 13.90 0 4 -11 213.78 11.30 -1 4 -11 -2.90 6.10 3 3 -11 47.60 9.20 2 3 -11 14.70 4.30 1 3 -11 2.40 3.30 0 3 -11 6.70 3.10 -1 3 -11 24.80 5.30 2 2 -11 255.47 14.30 1 2 -11 536.25 24.90 0 2 -11 1045.60 45.50 -1 2 -11 29.50 6.20 2 1 -11 222.68 13.30 1 1 -11 1369.86 59.09 0 1 -11 538.95 25.30 -1 1 -11 84.19 7.90 1 0 -11 130.19 10.00 0 0 -11 141.09 10.70 2 5 -12 129.39 11.90 2 4 -12 31.20 7.90 1 4 -12 56.89 6.40 1 3 -12 245.78 13.70 0 3 -12 71.79 7.00 0 2 -12 113.39 9.80 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 64308 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C002 C 0.37603(18) 0.40464(12) 0.29675(10) 0.01540(16) Uani 1 1 d . . . . . C003 C 0.2432(2) 0.30379(12) 0.08500(11) 0.01861(17) Uani 1 1 d . . . . . C004 C 0.36330(19) 0.63619(12) 0.41462(10) 0.01696(17) Uani 1 1 d . . . . . H004 H 0.2701 0.7271 0.3554 0.020 Uiso 1 1 calc R . . . . C005 C 0.48809(19) 0.73200(12) 0.61904(10) 0.01730(17) Uani 1 1 d . . . . . H005 H 0.4815 0.8898 0.7018 0.021 Uiso 1 1 calc R . . . . N001 N 0.1351(2) 0.22131(13) -0.08480(10) 0.02499(19) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C002 0.0157(3) 0.0175(3) 0.0124(3) 0.0060(2) -0.0001(2) 0.0024(2) C003 0.0210(3) 0.0192(3) 0.0149(3) 0.0068(2) -0.0004(2) 0.0036(2) C004 0.0193(3) 0.0177(3) 0.0148(3) 0.0075(2) -0.0003(2) 0.0043(2) C005 0.0200(3) 0.0163(3) 0.0147(3) 0.0055(2) 0.0001(2) 0.0042(2) N001 0.0327(4) 0.0240(3) 0.0159(3) 0.0065(2) -0.0033(2) 0.0057(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C004 C002 C003 119.27(6) . . ? C004 C002 C005 121.35(8) . 2_666 ? C005 C002 C003 119.38(7) 2_666 . ? N001 C003 C002 179.43(8) . . ? C002 C004 H004 120.5 . . ? C005 C004 C002 119.07(7) . . ? C005 C004 H004 120.5 . . ? C002 C005 H005 120.2 2_666 . ? C004 C005 C002 119.58(7) . 2_666 ? C004 C005 H005 120.2 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C002 C003 1.4343(13) . ? C002 C004 1.3919(13) . ? C002 C005 1.3971(12) 2_666 ? C003 N001 1.1513(12) . ? C004 H004 0.9500 . ? C004 C005 1.3820(13) . ? C005 C002 1.3971(12) 2_666 ? C005 H005 0.9500 . ?